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Technical Customer Support Specialist

June 9, 2026

Healthcare documentation is broken. Nestmed is fixing it with an AI platform that gives clinicians their time back.In just one year, we’ve scaled to support tens of thousands of clinicians across more than a million patient visits. We're now the trusted partner for over 60 home health agencies, including 7 of the top 10 enterprises in the US.Our founding team—hailing from Stanford, YC, Google, and Meta—is backed by the founders of PayPal and Plaid to build the essential infrastructure for the future of the $500B home healthcare industry.<h2>Technical Customer Support Specialist</h2>Location: Remote, based in Canada (EST hours)Type: Full-timeTeam: Customer ExperienceCompensation: CAD $80,000 - $90,000<h3></h3><h3>What You’ll Do</h3><ul style="min-height:1.5em"><li>Serve as the first line of support for our users, including clinicians, staff, and admins via Zendesk (email, chat, tickets, phone)</li><li>Troubleshoot user-reported issues, escalate bugs to product/engineering, and follow through on resolution</li><li>Triage and categorize inbound tickets to improve internal response speed and clarity</li><li>Translate user feedback into actionable insights to improve product usability</li><li>Collaborate closely with Customer Success to ensure a consistent and proactive support experience </li></ul><h3>What You Bring</h3><ul style="min-height:1.5em"><li>3+ years of experience in technical customer support or client-facing roles, ideally in a healthtech or healthcare SaaS company</li><li>Strong ability for technical troubleshooting and root cause analysis, being able to diagnose 'why' something isn't working</li><li>Ability to identify complex bugs and creating detailed reports for the Product and Engineering teams to fix.</li><li>Deep understanding of clinical workflows, home health, or EHR/EMR systems (bonus if you’ve worked with intake, charting, or QA)</li><li>Excellent written and verbal communication skills- you can simplify technical topics for non-technical users</li><li>Comfort with fast-changing environments and a bias toward action</li><li>Familiarity with ticketing softwares like Zendesk</li></ul><h3>Bonus Points For</h3><ul style="min-height:1.5em"><li>Knowledge of HIPAA compliance, security protocols, and protected health information (PHI)</li><li>Experience supporting an AI or voice-based product</li></ul><h3>Why Nestmed</h3><ul style="min-height:1.5em"><li>Mission-driven company improving healthcare documentation at scale</li><li>Early-stage team with huge ownership opportunities</li><li>Fast-growing customer base and real-world impact</li><li>Work closely with product and engineering teams to shape the user experience</li><li>Remote opportunity, collaborative culture, and meaningful work</li></ul><h3>Interview Process</h3><ul style="min-height:1.5em"><li>Initial Phone Screen</li><li>Hiring Manager Call</li><li>Take Home Assessment</li><li>Final Round + Virtual Meet and Greet! </li></ul>If you’re passionate about building high-impact products that solve real-world problems, we’d love to hear from you. Apply today!

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...